CA1160394A - Contenants en polyurethane - Google Patents

Contenants en polyurethane

Info

Publication number: CA1160394A
Authority: CA; Canada
Prior art keywords: polyester; dicarboxylic acid; mol percent; prepolymer; aliphatic
Prior art date: 1980-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000355035A

Other languages

English (en)

Inventor

Daniel A. Chung

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-06-27

Filing date

1980-06-27

Publication date

1984-01-10

1980-06-27 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1980-06-27 Priority to CA000355035A priority Critical patent/CA1160394A/fr

1984-01-10 Application granted granted Critical

1984-01-10 Publication of CA1160394A publication Critical patent/CA1160394A/fr

Status Expired legal-status Critical Current

Links

229920000728 polyester Polymers 0.000 title claims abstract description 37
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 15
239000000446 fuel Substances 0.000 claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 28
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 17
125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
-1 polyhexamethylene Polymers 0.000 claims abstract description 15
229920005862 polyol Polymers 0.000 claims abstract description 13
150000003077 polyols Chemical class 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 10
230000004888 barrier function Effects 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
239000007795 chemical reaction product Substances 0.000 claims abstract description 8
229920001228 polyisocyanate Polymers 0.000 claims abstract description 8
239000005056 polyisocyanate Substances 0.000 claims abstract description 8
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims abstract description 3
239000004814 polyurethane Substances 0.000 claims description 15
229920002635 polyurethane Polymers 0.000 claims description 14
150000004985 diamines Chemical class 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 7
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 7
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 5
125000002723 alicyclic group Chemical group 0.000 claims description 5
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
229920001971 elastomer Polymers 0.000 claims description 3
239000000806 elastomer Substances 0.000 claims description 3
229920001610 polycaprolactone Polymers 0.000 claims description 3
239000004632 polycaprolactone Substances 0.000 claims description 3
229920001634 Copolyester Polymers 0.000 claims description 2
229920003232 aliphatic polyester Polymers 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims 1
239000007859 condensation product Substances 0.000 abstract description 3
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 abstract 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 60
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
210000004027 cell Anatomy 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
239000004594 Masterbatch (MB) Substances 0.000 description 7
229940067597 azelate Drugs 0.000 description 7
239000012530 fluid Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
230000014759 maintenance of location Effects 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
150000003673 urethanes Chemical class 0.000 description 5
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004744 fabric Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
238000005266 casting Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
238000002791 soaking Methods 0.000 description 2
230000008961 swelling Effects 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
XLVAWGPBGMLWOQ-UHFFFAOYSA-N C(N)(O)=O.C(C)O.C(C)O Chemical compound C(N)(O)=O.C(C)O.C(C)O XLVAWGPBGMLWOQ-UHFFFAOYSA-N 0.000 description 1
102100023401 Dual specificity mitogen-activated protein kinase kinase 6 Human genes 0.000 description 1
101710146516 Dual specificity mitogen-activated protein kinase kinase 6 Proteins 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001536 azelaic acids Chemical class 0.000 description 1
239000004566 building material Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
238000007865 diluting Methods 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000012943 hotmelt Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002531 isophthalic acids Chemical class 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
210000002445 nipple Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
239000007962 solid dispersion Substances 0.000 description 1
210000000352 storage cell Anatomy 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000355035A 1980-06-27 1980-06-27 Contenants en polyurethane Expired CA1160394A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000355035A CA1160394A (fr)	1980-06-27	1980-06-27	Contenants en polyurethane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000355035A CA1160394A (fr)	1980-06-27	1980-06-27	Contenants en polyurethane

Publications (1)

Publication Number	Publication Date
CA1160394A true CA1160394A (fr)	1984-01-10

Family

ID=4117297

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000355035A Expired CA1160394A (fr)	1980-06-27	1980-06-27	Contenants en polyurethane

Country Status (1)

Country	Link
CA (1)	CA1160394A (fr)

1980
- 1980-06-27 CA CA000355035A patent/CA1160394A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-01-10	MKEX	Expiry

Publication	Publication Date	Title
US4247678A (en)	1981-01-27	Polyurethane derived from both an aliphatic dicarboxylic acid and an aromatic dicarboxylic acid and fuel container made therefrom
US5043381A (en)	1991-08-27	Aqueous dispersions of a nonionic, water dispersible polyurethane having pendent polyoxyethylene chains
US4182898A (en)	1980-01-08	Stable and storable polyester-polyether co-prepolymers
US4554308A (en)	1985-11-19	Crosslinked polyurethane dispersions
EP3887422B1 (fr)	2024-06-05	Procédé de préparation de dispersons de polyuréthane, substantiellement exempte de des composés organiques volatils et avec un extrait-sec élévé
US3721645A (en)	1973-03-20	Polyurethanes stabilized with 1,2,3-,1,2,4-1,2,5-,and 1,3,4-triazoles
US4487913A (en)	1984-12-11	Fuel and hydrolysis resistant polyurethane
US4574147A (en)	1986-03-04	Process for the production of polyurethanes, polyurethanes containing terminal aromatic amino groups and their use
US3718624A (en)	1973-02-27	Method of curing polyurethane prepolymers with liquid extender comprising 4,4{40 -methylenebis (2-chloroaniline) and low molecular weight polytetramethylene ether glycol
JPH01104613A (ja)	1989-04-21	水性分散物
EP0415177A2 (fr)	1991-03-06	Polyuréthanes pour des réservoirs de combustible souples
US20030220463A1 (en)	2003-11-27	Polyurethane dispersions
JPS6410552B2 (fr)	1989-02-22
US4496707A (en)	1985-01-29	Polyurethane and method for making stable components thereof
US20030027923A1 (en)	2003-02-06	High performance aqueous polyurethanes and methods of fabricating the same
US5097010A (en)	1992-03-17	Thermally-reversible isocyanate polymers
US4404258A (en)	1983-09-13	Color stabilized water-dispersed polyurethane coating on vinyl surfaces
US5852154A (en)	1998-12-22	Cold-curing, low-solvent or solvent-free 2-component polyurethane/polyurea compositions
CA2403195C (fr)	2008-09-09	Moulage par rotation pour depot d'un revetement sur un substrat flexible et article flexible a revetement ainsi obtenu
US4590254A (en)	1986-05-20	Non-aqueous poly(urethane-urea)
US4897430A (en)	1990-01-30	One Component polyurea
US3761452A (en)	1973-09-25	Epoxy polyurethane prepolymer compositions which are self curing uponapplication of heat
US3897400A (en)	1975-07-29	Polyurethane cured with an aromatic monosulfide diamine
EP1613678B1 (fr)	2011-07-27	Allongeur de chaine utile dans la production de polyurethannes et polyurethannes correspondants
CA1338718C (fr)	1996-11-12	Compositions de revetement a base d'urethane dans un solvant